Propylphosphonic anhydride → HCID 86723539, compound

HRID 2201307Notes

Reaction equation

HRID 2201307 reaction equation
C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.CCCP(O)(O)=O.[CH3:26][N:27]1[C:32]2=[CH:33][N:34]([CH2:43][CH2:44][CH2:45][C:46]([OH:48])=O)[C:35]([C:36]3[CH:37]=[C:38]([CH3:42])[CH:39]=[CH:40][CH:41]=3)=[C:31]2[C:30](=[O:49])[N:29]([CH3:50])[C:28]1=[O:51]>CN(C=O)C.C(OCC)(=O)C>[CH3:26][N:27]1[C:32]2=[C:33]3[N:34]([C:35]([C:36]4[CH:37]=[C:38]([CH3:42])[CH:39]=[CH:40][CH:41]=4)=[C:31]2[C:30](=[O:49])[N:29]([CH3:50])[C:28]1=[O:51])[CH2:43][CH2:44][CH2:45][C:46]3=[O:48]

Participants

6

Reactant 3

HCID 111923Propylphosphonic anhydrideHCID 204484Propylphosphonic acidHCID 86723537HCID 86723537, compound

Product 1

HCID 86723539HCID 86723539, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A solution of T3P® (1-propylphosphonic acid cyclic anhydride 50% solution in DMF) (1.0M, 329 μL, 0.56 mmol) was added to solid 4-(1,3-dimethyl-2,4-dioxo-5-m-tolyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)butanoic acid (step 2) (200 mg, 0.56 mmol), giving a paste. DMF (1 mL) was added and a solution formed. The solution was stirred at room temperature for 1 hour and at 100° C. for 1 hour. The reaction mixture was diluted with ethyl acetate (10 mL) and washed with sat. sodium bicarbonate (1×5 mL) and brine (3×5 mL). The organic phase was dried with magnesium sulfate and the solvent was removed under vacuum to give the title compound.

Workup

  1. customgiving a paste
  2. customa solution formed
  3. washwashed with sat. sodium bicarbonate (1×5 mL) and brine (3×5 mL)
  4. dry with materialThe organic phase was dried with magnesium sulfate
  5. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-0a5327f411ce489e88b2a832b855b55c
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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